US8629084B2ExpiredUtilityPatentIndex 73
Iodine-phenyl-substituted cyclic cetoenols
Est. expirySep 16, 2024(expired)· nominal 20-yr term from priority
Inventors:FISCHER REINERBRETSCHNEIDER THOMASILG KERSTINLEHR STEFANFEUCHT DIETERMALSAM OLGARECKMANN UDOBOJACK GUIDOARNOLD CHRISTIANAULER THOMASHILLS MARTIN JEFFREYKEHNE HEINZHEMPEL WALTRAUDSANWALD ERICH
C07C 233/52C07C 235/36C07D 493/10C07C 2601/14C07D 237/04C07D 207/36C07D 491/10C07D 307/94C07D 311/00C07C 57/58C07D 487/04C07D 307/60C07D 495/10C07D 209/54
73
PatentIndex Score
4
Cited by
175
References
11
Claims
Abstract
The invention relates to novel iodophenyl-substituted cyclic ketenols of the formula (I) in which CKE, J, X and Y are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly iodophenyl-substituted cyclic ketonols of the formula (I) and secondly at least one crop plant compatibility-improving compound.
Claims
exact text as granted — not AI-modifiedThe invention claimed is:
1. A compound of the formulae (I-1-a), (I-1-b) or (I-1-c):
Wherein
A, B, D, J, X and Y have the meanings given in the table:
Com-
pound
J
X
Y
D
A
B
I-1-a-1
2-I
H
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-2
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-3
2-I
4-CH 3
6-CH 3
H
—(CH 2 ) 2 —CHCH 3 —(CH 2 ) 2 —
I-1-a-5
2-I
5-CH 3
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-6
2-I
5-CH 3
H
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-a-7
2-I
4-Cl
6-C 2 H 5
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-a-8
2-I
4-Cl
6-C 2 H 5
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-10
3-I
6-CH 3
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-11
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-a-12
4-I
2-C 2 H 5
6-CH 3
H
CH 3
CH 3
I-1-a-13
4-I
2-C 2 H 5
6-CH 3
H
CH 3
I-1-a-14
4-I
2-C 2 H 5
6-CH 3
H
n-C 3 H 7
CH 3
I-1-a-15
4-I
2-C 2 H 5
6-CH 3
H
I-1-a-16
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 5 —
I-1-a-17
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 2 —CHCH 3 —(CH 2 ) 2 —
I-1-a-18
4-I
2-CH 3
6-CH 3
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-19
4-I
2-CH 3
6-CH 3
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-a-20
4-I
2-C 2 H 5
6-Cl
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-a-21
4-I
2-CH 3
6-CH 3
H
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-a-23
4-I
2-C 2 H 5
6-CH 3
H
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-a-24
4-I
2-C 2 H 5
6-Cl
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-a-26
4-I
2-C 2 H 5
6-CH 3
H
i-C 3 H 7
CH 3
I-1-a-27
4-I
2-C 2 H 5
6-CH 3
H
i-C 4 H 9
CH 3
wherein
A, B, D, R 1 , J, X and Y have the meanings given in the table:
Com-
pound
J
X
Y
D
I-1-b-1
2-I
5-CH 3
H
H
I-1-b-2
2-I
5-CH 3
H
H
I-1-b-3
2-I
4-Cl
6-C 2 H 5
H
I-1-b-4
2-I
4-Cl
6-C 2 H 5
H
I-1-b-5
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-6
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-7
4-I
2-CH 3
6-CH 3
H
I-1-b-8
4-I
2-CH 3
6-CH 3
H
I-1-b-9
4-I
2-CH 3
6-CH 3
H
I-1-b-10
4-I
2-CH 3
6-CH 3
H
I-1-b-11
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-12
4-I
2-C 2 H 5
6-Cl
H
I-1-b-13
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-14
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-15
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-16
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-17
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-18
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-19
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-20
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-21
4-I
2-C 2 H 5
6-CH 3
H
I-1-b-22
4-I
2-C 2 H 5
6-CH 3
H
Com-
pound
A
B
R 1
I-1-b-1
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-b-2
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
i-C 3 H 7
I-1-b-3
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
H 3 C—O—CH 2 —
I-1-b-4
—(CH 2 ) 2 —O—(CH 2 ) 2 —
H 3 C—O—CH 2 —
I-1-b-5
—(CH 2 ) 2 —O—(CH 2 ) 2 —
i-C 3 H 7
I-1-b-6
C 3 H 7
CH 3
i-C 3 H 7
I-1-b-7
—CH 2 —CH—OC 4 H 9 —(CH 2 ) 3 —
H 3 C—O—CH 2 —
I-1-b-8
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-b-9
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
Cl—CH 2 —
I-1-b-10
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-b-11
—(CH 2 ) 2 —O—(CH 2 ) 2 —
H 3 C—O—CH 2 —
I-1-b-12
—(CH 2 ) 2 —O—(CH 2 ) 2 —
H 3 C—O—CH 2 —
I-1-b-13
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
i-C 3 H 7
I-1-b-14
i-C 3 H 7
CH 3
i-C 3 H 7
I-1-b-15
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
H 3 C—O—CH 2 —
I-1-b-16
—(CH 2 ) 5 —
H 3 C—O—CH 2 —
I-1-b-17
—(CH 2 ) 5 —
i-C 3 H 7
I-1-b-18
CH 3
CH 3
i-C 3 H 7
I-1-b-19
—(CH 2 ) 5 —
t-C 4 H 9
I-1-b-20
i-C 3 H 7
CH 3
H 3 C—O—CH 2 —
I-1-b-21
CH 3
CH 3
H 3 C—O—CH 2 —
I-1-b-22
i-C 3 H 7
CH 3
i-C 3 H 7
wherein
A, B, D, M R 2 , J, X and Y have the meanings given in the table:
Compound
J
X
Y
D
A
B
I-1-c-1
4-I
2-CH 3
6-C 2 H 5
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-2
2-I
5-CH 3
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-4
2-I
5-CH 3
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-5
2-I
4-Cl
6-C 2 H 5
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-c-6
2-I
4-Cl
6-C 2 H 5
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-7
3-I
6-CH 3
H
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-8
4-I
2-CH 3
6-CH 3
H
—(CH 2 ) 2 —CHOCH 3 —(CH 2 ) 2 —
I-1-c-10
4-I
2-C 2 H 5
6-CH 3
H
n-C 3 H 7
CH 3
I-1-c-11
4-I
2-C 2 H 5
6-CH 3
H
CH 3
I-1-c-12
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-c-13
4-I
2-C 2 H 5
6-Cl
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
I-1-c-14
4-I
2-CH 3
6-CH 3
H
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-c-15
4-I
2-CH 3
6-CH 3
H
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-c-16
4-I
2-CH 3
6-CH 3
H
—CH 2 —CHOC 4 H 9 —(CH 2 ) 3 —
I-1-c-17
4-I
2-C 2 H 5
6-CH 3
H
—(CH 2 ) 5 —
I-1-c-18
4-I
2-C 2 H 5
6-CH 3
H
CH 3
CH 3
I-1-c-19
4-I
2-C 2 H 5
6-CH 3
H
i-C 4 H 9
CH 3
I-1-c-20
4-I
2-CH 3
6-CH 3
H
—(CH 2 ) 2 —O—(CH 2 ) 2 —
Compound
M
R 2
I-1-c-1
O
C 2 H 5
I-1-c-2
O
C 6 H 5 —CH 2 —
I-1-c-4
O
C 2 H 5
I-1-c-5
O
C 2 H 5
I-1-c-6
O
C 2 H 5
I-1-c-7
O
C 2 H 5
I-1-c-8
O
C 2 H 5
I-1-c-10
O
C 2 H 5
I-1-c-11
O
C 2 H 5
I-1-c-12
O
C 2 H 5
I-1-c-13
O
C 2 H 5
I-1-c-14
O
C 6 H 5 —CH 2 —
I-1-c-15
O
CH 2 ═CH—CH 2 —
I-1-c-16
O
C 2 H 5
I-1-c-17
O
C 2 H 5
I-1-c-18
O
C 2 H 5
I-1-c-19
O
C 2 H 5
I-1-c-20
O
C 2 H 5 .
2. The compound of claim 1 , wherein the compound is I-1-a-3, I-1-a-8, I-1-a-12, I-1-a-13, I-1-a-18, I-1-a-19, I-1-a-20, I-1-b-3, I-1-b-16, I-1-c-12, or I-1-c-17.
3. A compound of the formula (I-1-c-3):
4. A pesticide composition and/or herbicide composition comprising
at least one compound of claim 1 and; an extender and/or a surfactant.
5. A method for controlling an animal pest and/or unwanted vegetation, comprising
contacting one or more compounds of claim 1 with the pest, the unwanted vegetation, and/or their habitats.
6. A process for preparing a pesticide composition or a herbicide composition, comprising
mixing one or more compounds of claim 1 with an extender and/or a surfactant.
7. A composition comprising,
(a′) at least one compound of claim 1 ,
and
(b′) at least one crop plant compatibility-improving compound;
wherein the crop plant compatibility-improving compound is at least one of:
4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),
1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138),
4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),
1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl)
3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),
α-(cyanomethoximino)phenylacetonitrile (cyometrinil),
2,4-dichlorophenoxyacetic acid (2,4-D),
4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron),
3,6-dichloro-2-methoxybenzoic acid (dicamba),
S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),
2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24),
2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),
4,6-dichloro-2-phenylpyrimidine (fenclorim),
ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl),
phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),
4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim),
3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900),
ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl),
1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),
(4-chloro-o-tolyloxy)acetic acid (MCPA),
2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),
diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl)
2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),
2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),
1,8-naphthalic anhydride,
α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),
2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292),
3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),
3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),
4-(4-chloro-o-tolyl)butyric acid,
4-(4-chlorophenoxy)butyric acid,
diphenylmethoxyacetic acid,
methyl diphenylmethoxyacetate,
ethyl diphenylmethoxyacetate,
methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxy late,
ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,
ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate,
ethyl 5-phenyl-2-isoxazoline-3-carboxylate,
ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,
1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate,
4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,
1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate,
methyl 5-chloroquinoxaline-8-oxyacetate,
ethyl 5-chloroquinoline-8-oxyacetate,
allyl 5-chloroquinoxaline-8-oxyacetate,
2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate,
diethyl 5-chloroquinoline-8-oxymalonate,
diallyl 5-chloroquinoxaline-8-oxymalonate,
diethyl 5-chloroquinoline-8-oxymalonate,
4-carboxychroman-4-ylacetic acid (AC-304415),
4-chlorophenoxyacetic acid,
3,3′-dimethyl-4-methoxybenzophenone,
1-bromo-4-chloromethylsulfonylbenzene,
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,
1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,
N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,
and/or one of the following compounds
of the general formula (IIa)
the general formula (IIb)
and/or of the general formula (IIc)
wherein
m is 0, 1, 2, 3, 4 or 5,
A 1 represents one of the divalent heterocyclic groupings shown below:
n is 0, 1, 2, 3, 4 or 5,
A 2 represents optionally C 1 -C 4 -alkyl- and/or C 1 -C 4 -alkoxy-carbonyl- and/or C 1 -C 4 -alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
R 14 represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,
R 15 represents hydroxyl, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,
R 16 represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl,
R 17 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,
R 18 represents hydrogen, in each case an fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,
R 17 and R 18 also together represent C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which may be optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,
R 19 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
R 20 represents hydrogen, in each case an optionally hydroxyl-, cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 3 -C 6 -cycloalkyl or tri-(C 1 -C 4 -alkyl)-silyl,
R 21 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
X 1 represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
and/or the following compounds
of the general formula (IId)
or of the general formula (IIe)
wherein
t is 0, 1, 2, 3, 4 or 5,
v is 0, 1, 2, 3, 4 or 5,
R 22 represents hydrogen or C 1 -C 4 -alkyl,
R 23 represents hydrogen or C 1 -C 4 -alkyl,
R 24 represents hydrogen, in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino, or in each case optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino,
R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl,
R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted phenyl, or together with R 25 represents in each case optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,
X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, and
X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.
8. The composition as claimed in claim 7 , wherein the crop plant compatibility-improving compound comprises at least one of
cloquintocet-mexyl,
fenchlorazole-ethyl,
isoxadifen-ethyl,
mefenpyr-diethyl,
furilazole,
fenclorim,
cumyluron,
dymron,
compound IIe-5, or
compound IIe-11;
wherein the compounds IIe-5 or IIe-11 have the following formulae:
9. The composition of claim 7 , wherein the crop plant compatibility-improving compound is mefenpyr-diethyl.
10. A method for controlling unwanted vegetation, comprising contacting the composition of claim 7 with the vegetation or its habitat.
11. A method for controlling unwanted vegetation, comprising contacting a compound of claim 1 and a crop plant compatibility-improving compound, separately in close temporal succession, or as a mixture, with the unwanted vegetation or its habitat;
wherein the crop plant-compatibility-improving compound is at least one of:
4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),
1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138),
4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),
1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl),
3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),
α-(cyanomethoximino)phenylacetonitrile (cyometrinil),
2,4-dichlorophenoxyacetic acid (2,4-D),
4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron),
3,6-dichloro-2-methoxybenzoic acid (dicamba),
S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),
2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24),
2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),
4,6-dichloro-2-phenylpyrimidine (fenclorim),
ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl),
phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),
4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim),
3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900),
ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxy late (isoxadifen-ethyl),
1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),
(4-chloro-o-tolyloxy)acetic acid (MCPA),
2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),
diethyl 1-(2,4-dichorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl),
2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),
2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),
1,8-naphthalic anhydride,
α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),
2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292),
3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),
3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),
4-(4-chloro-o-tolyl)butyric acid,
4-(4-chlorophenoxy)butyric acid,
diphenylmethoxyacetic acid,
methyl diphenylmethoxyacetate,
ethyl diphenylmethoxyacetate,
methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,
ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate,
ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate,
ethyl 5-phenyl-2-isoxazoline-3-carboxylate,
ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate,
1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate,
4-allyloxybutyl 5-chloroquinoline-8-oxyacetate,
1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate,
methyl 5-chloroquinoxaline-8-oxyacetate,
ethyl 5-chloroquinoline-8-oxyacetate,
allyl 5-chloroquinoxaline-8-oxyacetate,
2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate,
diethyl 5-chloroquinoline-8-oxymalonate,
diallyl 5-chloroquinoxaline-8-oxymalonate,
diethyl 5-chloroquinoline-8-oxymalonate,
4-carboxychroman-4-ylacetic acid (AC-304415),
4-chlorophenoxyacetic acid,
3,3′-dimethyl-4-methoxybenzophenone,
1-bromo-4-chloromethylsulfonylbenzene,
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,
1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,
N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide,
and/or one of the following compounds
of the general formula (IIa)
the general formula (IIb)
and/or of the general formula (IIc)
wherein
m iso, 1, 2, 3, 4 or 5,
A 1 represents one of the divalent heterocyclic groupings shown below:
n is 0, 1, 2, 3, 4 or 5,
A 2 represents optionally C 1 -C 4 -alkyl- and/or C 1 -C 4 -alkoxy-carbonyl- and/or C 1 -C 4 -alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
R 14 represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,
R 15 represents hydroxyl, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino,
R 16 represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl,
R 17 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,
R 18 represents hydrogen, in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or an optionally fluoro, chloro or bromo- or C 1 -C 4 -alkyl-substituted phenyl,
R 17 and R 18 also together represent C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which may be optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are attached, form a 5- or 6-membered carbocycle,
R 19 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
R 20 represents hydrogen, in each case an optionally hydroxyl-, cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri-(C 1 -C 4 -alkyl)-silyl,
R 21 represents hydrogen, cyano, halogen, or represents in each case an optionally fluoro, chloro or bromo-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
X 1 represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
X 2 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C1-C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
and/or the following compounds,
of the general formula (IId)
or of the general formula (IIe)
wherein
t is 0, 1, 2, 3, 4 or 5,
v is 0, 1, 2, 3, 4 or 5,
R 22 represents hydrogen or C 1 -C 4 -alkyl,
R 23 represents hydrogen or C 1 -C 4 -alkyl,
R 24 represents hydrogen, in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di(C 1 -C 4 -alkyl)-amino, or in each case optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino,
R 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl,
R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted phenyl, or together with R 25 represents in each case optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,
X 4 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, and
X 5 represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.Cited by (0)
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